18631-68-0

Usage

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 1205, 1980 DOI: 10.1016/S0040-4039(00)71371-2Synthesis, p. 529, 1984 DOI: 10.1055/s-1984-30893

Upstream product

• 625-35-4 trans-chrotonyl chloride 
• 107-93-7 (E)-but-2-enoic acid 
• 110-83-8 cyclohexene 
• 17874-17-8 cyclohex-1-enyl-trimethyl-silane 
• 103273-78-5 1-Methyl-hexahydroindanol-⁽⁹⁾-on-⁽³⁾ 
• 28817-28-9 3-(2-oxo-cyclohexyl)-butyric acid 
• 91897-80-2 1-(1'-cyclohexenyl)-2-buten-1-one 
• 72252-20-1 1-(1'-acetoxycyclohexyl)-2-buten-1-one 
• 16466-27-6 4-methyl-5-cyclohexyl-2-tetrahydrofuranone 
• 126231-52-5 (E)-1-trimethylsilyl-4-(1-cyclohexenyl)-1-buten-3-yne 
• 108-94-1 cyclohexanone 
• 31416-78-1 (2E)-2-butenoic acid, cyclohexyl ester 
• 15450-53-0 propenyl Δ¹-cyclohexenyl ketone 
• 69849-15-6 1-(1'-hydroxycyclohexyl)-2-buten-1-one 

Downstream Products

• 857505-15-8 1-phenyl-3-methyl-4,5,6,7-tetrahydroindene 
• 767-58-8 1-methylindane 

Relevant academic research and scientific papers

Palladium-catalyzed tandem oxidative cyclization of 1-bromohexa-1,5-dien-3- ols: Easy access to cyclopentenones

The novel Pd-catalyzed tandem cyclization of 1-bromohexa-1,5-dien-3-ols, prepared from the corresponding β-bromo-vinylaldehydes to cyclopentenone derivatives has been developed.

Silacycle-Templated Intramolecular Diels-Alder Cyclizations for the Diastereoselective Construction of Complex Carbon Skeletons

The utility of the dioxasiline ring as a π-facial directing group in the intramolecular Diels-Alder cyclization is explored. An initial investigation of substrate scope demonstrates that the rigidity of this directing group delivers robust stereocontrol across a number of substrates, affording single diastereomers in moderate to good yields. A mechanistic investigation reveals that the reactive diene is formed through γdeprotonation followed by [1,5] hydride shifts.

Palladium-catalyzed novel cycloisomerization: An unprecedented domino oxidative cyclization towards substituted carbocycles

Efficient Pd-catalyzed cyclization of homoallylated β-bromo- vinylalcohols via a domino process to carbocycle derivatives in presence of different bases is reported. An unexpected and novel palladium-mediated Heck-type intramolecular oxidative cyclization

Synthesis and properties of novel substituted 4,5,6,7-tetrahydroindenes and selected metal complexes

The synthesis of a complete series of substituted 4,5,6,7-tetrahydroindenes (4,5,6,7-tetrahydroindene, 1; 1-methyl-, 1,3-dimethyl- and 1,2,3-trimethyl-4,5,6,7-tetrahydroindene, 2-4) is reported.The synthesis of ferrocenes (8-11) from these substituted cyclopentadienes is described.The electrochemistry of these ferrocenes indicates that these complexes are more readily oxidized than ferrocene and that the effect of methyl or alkyl substituents on the ease of oxidation is additive.A single crystal X-ray structure of two of the ferrocenes, bis(1,3-dimethyl-4,5,6,7-tetrahydroindenyl)iron(II), 10, and bis(1,2,3-trimethyl-4,5,6,7-tetrahydroindenyl)iron(II), 11, indicates that steric hindrance causes the alkyl substituents to be bent away from the plane of the cyclopentadienyl ring.However, the structures differ in that the cyclopentadienyl rings in 10 are staggered whereas those in 11 are eclipsed.The synthesis of the cyclopentadienyltricarbonylmethyl compounds of molybdenum and tungsten from 3 and 4 is also described.Keywords: Iron; Molybdenum; Tungsten; Indenes; Metallocenes; Electrochemistry

Vinylsilane mediated regiospecific cyclopentenone annulation of ketones

The development of a new cyclopentenone annulation sequence of general scope which involves Friedel-Crafts acylation of a vinylsilane with an α,β-unsaturated acid chloride followed by Nazarov cyclization is reported.

SYNTHESIS OF SUBSTITUTED CYCLOPENTADIENE COMPOUNDS AND METALLOCENES

A method of synthesizing a substituted cyclopentadiene compound. The synthesis comprises a step of cyclizing, in the presence of a phosphorous pentoxide/methanesulfonic acid reagent, an alpha,beta-unsaturated carboxylic acid, cycloalkyl ester compound to

SYNTHESIS OF CYCLOPENTENONES

A method comprising synthesizing a substituted cyclopentenone compound via reaction of a substituted cycloalkyl acrylate ester in the presence of phosphorous pentoxide/methanesulfonic acid reagent to make the substituted cyclopentenone compound.

SYNTHESIS OF CYCLIC ORGANIC COMPOUNDS AND METALLOCENES

A method comprising synthesizing a cyclic organic compound via reaction of an unsubstituted or substituted cyclohexene with an unsubstituted or substituted acrylic acid in the presence of phosphoric and/or sulfonic acid reagent to make the cyclic organic compound. Also, a method of synthesizing a ligand for a transition metal, and a related substituted ligand-metal complex and catalyst, from the unsubstituted or substituted cyclohexene and unsubstituted or substituted acrylic acid. Also, the cyclic organic compound, ligand, and substituted ligand-metal complex and catalyst synthesized thereby. Also a method of polymerizing an olefin with the catalyst to give a polyolefin, and the polyolefin made thereby.

Correlating reactivity and selectivity to cyclopentadienyl ligand properties in Rh(III)-catalyzed C-H activation reactions: An experimental and computational study

CpxRh(III)-catalyzed C-H functionalization reactions are a proven method for the efficient assembly of small molecules. However, rationalization of the effects of cyclopentadienyl (Cpx) ligand structure on reaction rate and selectivity has been viewed as a black box, and a truly systematic study is lacking. Consequently, predicting the outcomes of these reactions is challenging because subtle variations in ligand structure can cause notable changes in reaction behavior. A predictive tool is, nonetheless, of considerable value to the community as it would greatly accelerate reaction development. Designing a data set in which the steric and electronic properties of the CpxRh(III) catalysts were systematically varied allowed us to apply multivariate linear regression algorithms to establish correlations between these catalyst-based descriptors and the regio-, diastereoselectivity, and rate of model reactions. This, in turn, led to the development of quantitative predictive models that describe catalyst performance. Our newly described cone angles and Sterimol parameters for Cpx ligands served as highly correlative steric descriptors in the regression models. Through rational design of training and validation sets, key diastereoselectivity outliers were identified. Computations reveal the origins of the outstanding stereoinduction displayed by these outliers. The results are consistent with partial η5-η3 ligand slippage that occurs in the transition state of the selectivity-determining step. In addition to the instructive value of our study, we believe that the insights gained are transposable to other group 9 transition metals and pave the way toward rational design of C-H functionalization catalysts.

Palladium-catalyzed intramolecular oxidative heck cyclization and its application toward a synthesis of (±)-β-cuparenone derivatives supported by computational studies

A novel and efficient intramolecular oxidative cyclization of substituted homoallylic alcohols to form cyclic keto compounds under palladium-catalyzed conditions is described. The reaction has practical applications in the synthesis of sesquiterpenes. The